I am a huge fan of a number of our green spaces in the city. Tommy Thompson park, Biidisaage, and Taylor Creek/the Don Valley trails are all fantastic and not as well known as the ones in the West end. Biidissage only opened up over the last year or two, and it's reconnected the Don River to the lake and it's beautifully done and designed.
Partner and I recently went to the FreePlay Arcade Bar for the first time and really enjoyed it. They've got some good pinball options. It's near College and Spadina.
Food!
I had two other reccs originally (Mahas and Dil Se Indian), and I still stand by them but they're def known to be great. Mahas (Egyptian food) you have to show up early cuz they don't do reservations.
Two places near Greenwood/Coxwell stations:
Tata's Jerk Chicken. Just get the regular sandwich, don't change anything. Get it cut in half. It's so good. They're shut on Sundays as a heads up.
Pomarosa, it's Venezuelan and they have delicious arepas.
Not husband, fiancee, and they've not been together a full year yet. He says he's a democrat, but has donated to Republicans as well (Susan Collins just last year, to name one, and it was over 24k).